Synthesis of thermoresponsive oxazolone end-functional polymers for reactions with amines using thiol-Michael addition "click" chemistry

被引：24

作者：

Ho, The Hien ^{[1
]}

Levere, Martin ^{[1
]}

Soutif, Jean-Claude ^{[1
]}

Montembault, Veronique ^{[1
]}

Pascual, Sagrario ^{[1
]}

Fontaine, Laurent ^{[1
]}

机构：

[1] Univ Maine, CNRS, UCO2M, UMR 6011, F-72085 Le Mans, France

来源：

POLYMER CHEMISTRY | 2011年 / 2卷 / 06期

关键词：

LIVING RADICAL POLYMERIZATION; ORTHOGONAL SYNTHESIS; ALKENYL AZLACTONES; YNE REACTIONS; ROUTE;

D O I：

10.1039/c1py00071c

中图分类号：

O63 [高分子化学（高聚物）];

学科分类号：

070305 ; 080501 ; 081704 ;

摘要：

Well-defined poly(N-isopropylacrylamide) (PNIPAM) polymers with an oxazolone ring at the chain end have been synthesized by combining controlled radical polymerization and thiol-Michael addition "click" chemistry. First, PNIPAM was synthesized using reversible addition-fragmentation chain transfer (RAFT) polymerization to afford polymers of controlled molecular weight and molecular weight distribution (M-n (1H NMR) = 3200 g mol(-1); PDISEC = 1.05). The chain end was quantitatively converted to a thiol by aminolysis. Then, the functional monomer vinyl azlactone (VDM) was quantitatively "clicked" onto the chain end using a thiol-Michael addition reaction. The polymers were reacted with a model amine in order to demonstrate the potential of these polymers for bioconjugation.

引用

页码：1258 / 1260

页数：3

共 33 条

[1] The Thiol-Michael Addition Click Reaction: A Powerful and Widely Used Tool in Materials Chemistry
Nair, Devatha P.
Podgorski, Maciej
Chatani, Shunsuke
Gong, Tao
Xi, Weixian
Fenoli, Christopher R.
Bowman, Christopher N.
[J]. CHEMISTRY OF MATERIALS, 2014, 26 (01) : 724 - 744
[2] Combinatorial synthesis of functional polymers with complex architectures using thiol-Michael and aza-Michael chemistries
Love, Dillon
Domaille, Dylan
Fairbanks, Benjamin
Klug, David
Bowman, Christopher
[J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2018, 256
[3] Light Harvesting Modulation of Melanin-Like Polymers via Thiol-Michael "Click" Chemistry
Zou, Yuan
Liu, Huijie
Wang, Xianheng
Xu, Yuanting
Yang, Ye
Bai, Wanjie
Li, Yiwen
[J]. MACROMOLECULES, 2023, 56 (23) : 9530 - 9539
[4] Fabrication of micropatterned gold nanoparticles on graphene oxide nanosheet via thiol-Michael addition click chemistry
Nie, Lei
Zhang, Jingjing
Wu, Qiaoyun
Fei, Guanghai
Hu, Kehui
Fang, Liang
Yang, Shoufeng
[J]. MATERIALS LETTERS, 2020, 261
[5] Functionalizable thermoresponsive polymers synthesized from renewable 5-hydroxymethylfurfural derivative via the thiol-Michael addition reaction
Zhang, Daihui
Dumont, Marie-Josee
[J]. POLYMER, 2018, 145 : 157 - 161
[6] Synthesis and characterization of end-functional polymers on silica nanoparticles via a combination of atom transfer radical polymerization and click chemistry
Wang, Yunpu
Chen, Jiucun
Xiang, Jiming
Li, Hongjun
Shen, Yongqian
Gao, Xianghu
Liang, Yan
[J]. REACTIVE & FUNCTIONAL POLYMERS, 2009, 69 (06): : 393 - 399
[7] A straightforward approach for the one-pot synthesis of cyclic polymers from RAFT polymers via thiol-Michael addition
Zhao, Junfei
Zhou, Yanyan
Zhou, Yu
Zhou, Nianchen
Pan, Xiangqiang
Zhang, Zhengbiao
Zhu, Xiulin
[J]. POLYMER CHEMISTRY, 2016, 7 (09) : 1782 - 1791
[8] POLY 507-Biotin end-functional star polymers via TMM LRP and click chemistry
Cauet, Solene
Mantovani, Giuseppe
Ladmiral, Vincent
Haddleton, David M.
[J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 234
[9] Combining atom transfer radical polymerization and click chemistry:: A versatile method for the preparation of end-functional polymers
Lutz, JF
Börner, HG
Weichenhan, K
[J]. MACROMOLECULAR RAPID COMMUNICATIONS, 2005, 26 (07) : 514 - 518
[10] Kinetics of Polymer Interfacial Reactions: Polymer Brush Formation by Click Reactions of Alkyne End-Functional Polymers with AzideFunctional Substrates
Zhang, Shuo
Vi, Thu
Luo, Kai
Koberstein, Jeffrey T.
[J]. MACROMOLECULES, 2016, 49 (15) : 5461 - 5474

← 1 2 3 4 →